42096-33-3

Basic information

• Product Name: 2-methylphenyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate
• CAS NO: 42096-33-3
• Molecular Formula: C₁₁H₇F₉O₃S
• Molecular Weight: 390.2221
• Mol File: 42096-33-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 286.4°C at 760 mmHg
• Flash Point: 127°C
• Density: 1.564g/cm³
• Vapor Pressure: 0.00455mmHg at 25°C
• Refractive Index: 1.408
• CAS DataBase Reference: 2-methylphenyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methylphenyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate(42096-33-3)
• EPA Substance Registry System: 2-methylphenyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate(42096-33-3)

Safety Data

• Hazardous Substances Data: 42096-33-3(Hazardous Substances Data)

Upstream product

• 375-72-4 Nonafluorobutanesulfonyl fluoride 
• 95-48-7 ortho-cresol 
• 4549-72-8 sodium o-cresolate 
• 16419-60-6 2-Methylphenylboronic acid 
• 29420-49-3 potassium nonaflate 

Downstream Products

• 108-88-3 toluene 
• 54560-76-8 N-(2-methylphenyl)-n-hexylamine 
• 1205-39-6 N-phenyl-2-methylaniline 
• 1262210-32-1 (Z)-1-(1-(4-methoxyphenyl)prop-1-en-1-yl)-2-methylbenzene 
• 1262210-27-4 2-methoxy-2'-methyl-2,3,4,5-tetrahydro-1,1'-biphenyl 
• 1985-77-9 (Z)-(1-(o-tolyl)ethene-1,2-diyl)dibenzene 
• 83135-54-0 (E)-1-methyl-2-(3-phenylprop-1-en-1-yl)benzene 
• 1262210-33-2 (Z)-1-methyl-2-(1-phenylbut-1-en-1-yl)benzene 
• 80-28-4 N-(2-methylphenyl)-p-toluenesulphonamide 
• 1255365-30-0 2-methyl-N-morpholinobenzenesulfonamide 
• 130250-61-2 2-methyl-N-methoxy-N-methylbenzamide 
• 6840-26-2 diphenyl-o-tolyl-phosphine oxide 

Relevant articles and documents

Palladium-Catalyzed C-P Bond-Forming Reactions of Aryl Nonaflates Accelerated by Iodide

An iodide-accelerated, palladium-catalyzed C-P bond-forming reaction of aryl nonaflates is described. The protocol was optimized for the synthesis of aryl phosphine oxides and was found to be tolerant of a wide range of aryl nonaflates. The general nature of this transformation was established with coupling to other P(O)H compounds for the synthesis of aryl phosphonates and an aryl phosphinate. The straightforward synthesis of stable, isolable aryl nonaflates, in combination with the rapid C-P bond-forming reaction allows facile preparation of aryl phosphorus target compounds from readily available phenol starting materials. The synthetic utility of this general strategy was demonstrated with the efficient preparation of an organic light-emitting diode (OLED) material and a phosphonophenylalanine mimic.

A general method for palladium-catalyzed reactions of primary sulfonamides with aryl nonaflates

A general method for Pd-catalyzed sulfonamidation of aryl nonafluorobutanesulfonates (aryl nonaflates) is described. A biaryl phosphine ligand, t-BuXPhos, formed the most active catalyst, and K3PO 4 in tert-amyl alcohol was found to be the optimal base-solvent combination for the reaction. The reaction conditions were tolerant of various functional groups such as cyano, nitro, ester, aldehyde, ketone, chloride, carbamate, and phenol. Heterocyclic aryl nonaflates were found to be suitable coupling partners. High yields of the coupled products were obtained from the reactions between inherently disfavored substrates such as electron-rich nonaflates and electron-poor sulfonamides. Kinetic data suggest reductive elimination to be the rate-limiting step for the reaction. The only limitation of this methodology that we have identified is the inability of 2,6-disubstituted aryl nonaflates to efficiently participate in the reaction.

Palladium-Catalyzed Amination of Aryl Nonaflates

The first detailed study of the palladium-catalyzed amination of aryl nonaflates is reported. Use of ligands 2-4 and 6 allows for the catalytic amination of electron-rich and -neutral aryl nonaflates with both primary and secondary amines. With use of Xantphos 5, the catalytic amination of a variety of functionalized aryl nonaflates resulted in excellent yields of anilines; even 2-carboxymethyl aryl nonaflate is effectively coupled with a primary alkylamine. Moderate yields were obtained when coupling halo-aryl nonaflates with a variety of amines, where in most cases the aryl nonaflate reacted in preference to the aryl halide. Overall, aryl nonaflates are an effective alternative to triflates in palladium-catalyzed C-N bond-forming processes due to their increased stability under the reaction conditions.